Chapter-0i Types of Org RXN

Al-Imam Muhammad ibn Saud Isalmic University
Department of Chemistry CHEM 327 – Organic Reactions Mechanisms
Organic Reactions Mechanisms (CHEM 327)

Dr. Abdulrahman Alhamzani & Dr. Wessam Abdulfatah
Course Description:
This course provides students with an Introduction for Organic Reactions Mechanism, which
covers all aspects; kinetic and physical methods to determine organic reaction mechanism;
classifications of reaction mechanism; Substitution; Addition; Elimination; Radical Addition
Reaction and Rearrangement.
Grading for this Course:

Exam 1: 20 % Exam 2: 20 % Final Exam: 40 %
Quizzes; Homework & Attendance & Participation: 20 %
Text Book:
Writing Reactions Mechanisms in Organic Chemistry, By: Audrey Miller & Philippa Solomon
ISBN: 0124967124, Publisher: Elsevier Science & Technology Books.
1
Overview of Organic Reactions

There are 4 general types of organic
reactions
2
3
4
5
There are two ways in which a covalent two-electron bond can break.
The movement of one electron in the symmetrical process is indicated using a halfheaded,
or “fishhook,” arrow
The movement of two electrons in the unsymmetrical process is indicated using a full-headed
curved arrow 6
there are two ways in which a covalent two-electron bond can form.
Processes that involve symmetrical bond-breaking and bond-making are called

radical reactions.
A radical, often called a “free radical,” is a neutral chemical species that contains an
odd number of electrons and thus has a single, unpaired electron in one of its
orbitals.
Processes that involve unsymmetrical bond-breaking and bond-making are called

polar reactions.
Polar reactions involve species that have an even number of electrons and thus have
only electron pairs in their orbitals.
7
Most organic compounds are electrically neutral; they have no net charge, either positive or
negative.
Bond polarity is a consequence of an unsymmetrical electron distribution in a bond and is due

to the difference in electronegativity of the bonded atoms.
Elements such as oxygen, nitrogen, fluorine, and chlorine are more electronegative than
carbon, so a carbon atom bonded to one of these atoms has a partial positive charge (δ+).
Conversely, metals are less electronegative than carbon, so a carbon atom bonded to a metal
has a partial negative charge (δ-).
Electrostatic potential maps
8
In neutral methanol, the carbon atom is somewhat electron-poor because the

electronegative oxygen attracts the electrons in the C-O bond. On protonation of the
methanol oxygen by an acid, however, a full positive charge on oxygen attracts the
electrons in the C-O bond much more strongly and makes the carbon much more electron-
poor.
9
10
11
Chemists indicate the movement of an electron pair during a polar reaction by using a curved,
full-headed arrow. A curved arrow shows where electrons move when reactant bonds are
broken and product bonds are formed. This means that an electron pair moves from the atom
(or bond) at the tail of the arrow to the atom at the head of the arrow during the reaction.
A nucleophile: is a substance that is “nucleus-loving.” (Remember that a nucleus is

positively charged.) A nucleophile has a negatively polarized, electron-rich atom and can
form a bond by donating a pair of electrons to a positively polarized, electronpoor atom.
An electrophile, is “electron-loving.” An electrophile has a positively polarized,

electronpoor atom and can form a bond by accepting a pair of electrons from a
12
nucleophile. Electrophiles can be either neutral or positively charged.
Some Nucleophiles: (Electron-rich)
Some Electrophiles: (Electron-poor)
13
14
15
What do we know about ethylene? We know that a carbon–carbon double bond results from
the orbital overlap of two sp2-hybridized carbon atoms. The σ part of the double bond results
from sp2–sp2 overlap, and the part results from p–p overlap.
What kind of chemical reactivity might we expect from a C=C bond? We know that alkanes,
such as ethane, are relatively inert because all valence electrons are tied up in strong, nonpolar,
C-C and C-H bonds. Furthermore, the bonding electrons in alkanes are relatively inaccessible to
approaching reactants because they are sheltered in s bonds between nuclei.
16
Figure 5-2 A comparison of carbon–carbon single and double bonds. A double bond is both
more accessible to approaching reactants than a single bond and more electron-rich (more
nucleophilic). An electrostatic potential map of ethylene indicates that the double bond is the
region of highest negative charge.
17
18
19
20
21
22
23
24
25

Chapter-0i Types of Org RXN

Uploaded by

Document Information

Original Description:

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Chapter-0i Types of Org RXN

Uploaded by

Copyright:

Available Formats

Al-Imam Muhammad ibn Saud Isalmic University

Department of Chemistry CHEM 327 – Organic Reactions Mechanisms

Organic Reactions Mechanisms (CHEM 327)

Grading for this Course:

Overview of Organic Reactions

Processes that involve symmetrical bond-breaking and bond-making are called

Processes that involve unsymmetrical bond-breaking and bond-making are called

Bond polarity is a consequence of an unsymmetrical electron distribution in a bond and is due

In neutral methanol, the carbon atom is somewhat electron-poor because the

A nucleophile: is a substance that is “nucleus-loving.” (Remember that a nucleus is

An electrophile, is “electron-loving.” An electrophile has a positively polarized,

Some Nucleophiles: (Electron-rich)

Some Electrophiles: (Electron-poor)

You might also like